Scintillating 2019 Fantasy Fest Schedule of Events Calendar

The 2019 Fantasy Fest Schedule of Events in Key West FL is guaranteed to thrill, titillate, tantalize and tempt you like never before!

The theme for 2019 Key West Fantasy Fest is "In Tune but Off Key: Celebrating 40 Years of Fantasy"!

As in year's past, the 2019 Fantasy Fest theme will have a lot of room for your imagination to run as wild as your desires.

Don't be tempted to play safe and just run with the theme.

Unleash your inhibition and your vocal cords as the potential for fun is endless. Who's your favorite musician or group? Who do you want to mimic in style - dress, hair, shoes, vocal capability?

Put your thinking cap on, and become the most exotic, provocative, and exciting 'musician/entertainer" you can possibly be at this year's Key West Fantasy Fest party!

For some of the sexiest and best festival costumes, don't miss out on fun, hot styles for you and your pets at our costume store.

To help you find what you need, you'll see throughout this page we've selected costumes covering a broad range of styles and themes. We've also included comic and movie related characters, devilish and horror related costumes, and others that are equally appropriate for various phases of Fantasy Fest and the different parties being held!

The various costume layouts below will give you quick access to a variety of costumes so you can envision what you may want to wear while you're at Fantasy Fest or any other fun party event.

All the costumes seen on this page are able to be presented to you as I am an affiliate of Halloween Costumes and an Amazon Associate and as such I earn from qualifying purchases. None of these items cost you any more if you purchase here, this is what being called an "affiliate" means.


So go ahead and mark Friday, October 18 through to October 27 on your calendar so you don't miss out on the highly anticipated 2019 Key West Fantasy Fest.

Also, the following Fantasy Fest Calendar of Events will help you plan which events you won't want to miss. This will help you make sure you have the right Fantasy Fest costumes needed to attend the biggest Key West party faithfully held each year, and that you have the necessary tickets when required.

The key to having fun at the 2019 Key West Fantasy Fest is to let your imagination run wild! Be creative and let your costumes tell the story of who you are, and dare to make this year the sexiest Fantasy Fest ever!

If you're at a loss for what to wear, and don't want to be caught without a sufficient wardrobe, don't worry. We have a solution that will be sure to please even the sultriest vixen.

Now is the time to start planning some of your Fantasy Festival costumes. You're going to want to wear costumes that make you stand out from the crowd when you attend all, or even part of the 10 day sextravaganza.

This means you'll want to gather up a number of Fantasy Fest costume ideas that fit both this years theme and the various Key West party events. Buy costumes that will suit who you are, then embellish them to create a total YOU.

You're better off to have at least a few Fantasy Fest costumes sexy enough to wear. Remember, you want to be a part of the event not just a spectator.

You'll also need to make your Fantasy Fest plans as soon as possible. Popular Key West events that require tickets can sell out quickly. Also Key West accommodations can become difficult to find at the last minute.


French Maids at Garden of Eden Bull and Whistle Bar

 

French Maids at the Garden of Eden, Bull and Whistle Bar
Photo Courtesy of Roy Llowarch on Flickr


Remember, sexy only has to be as sexy as you're comfortable with, but this hot Key West event is a chance for you to get a little risque without going overboard if you don't want to.

The following Key West events calendar highlights the riotous parties so you can pick which of the Key West Fantasy Fest Schedule of Events you'll attend October 18 - October 27.












Ongoing Fantasy Fest Events

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

Tickets and information available at https://www.waterfrontplayhouse.org   

BART 

The new daily Fantasy Fest Event is BART! The official Bar & Art Stroll which is a do-it-yourself guided walk that takes you to the fun and beautiful Historic Seaport located between Conch Republic Seafood Company and Dante's.  

Plan stops at Half Shell Raw Bar, Turtle Kraals, Waterfront Brewery, Schooner Wharf Bar and The Marker. You will also want to check in at participating bars with #BARTKW plus a photo of the figures and sculptures so you could win vintage Fantasy Fest t-shirts and swag!

DRESS LIKE ELVIS GET A DISCOUNT 

Key West party goers who dress like Elvis and go to the Two Friends Patio during the 10 days of Fantasy Fest will get the added bonus of 15% off their check. Two Friends Patio, 512 Front St, 305-296-3124

FAIRVILLA FOR SEXY, FUN COSTUMES AND ACCESSORIES

Shop for everything your hear desires and make Fantasty Fest complete with a huge array of 'dress up' material from wigs to costumes. 11 am - Midnight, 524 Front St.

FANTASTIC BODY PAINTING AND STUNNING SUNSETS:
FEMME FATALE QUATRE BODY ART AT SUNSET PIER 

Femme Fatale Quatre Body Art, the popular all girl group of body artists, will turn you into a canvas to be envied and drooled over. Choose from tiny artistic dabblings to full body makeovers!

Walkups are possible most days, but to be safe, book in advance by calling or texting 1-850-596-4065, 0 Duval Street Sunset Pier

FURY WATER ADVENTURES DISCOUNT

This popular Key West adventure company is offering Fantasy Fest party goers 10% off select day trips with promo code FANTASY*. 

Adventure trips available include Parasail, Jet Ski Tour, Glass Bottom Boat Eco Tour, Reef & Ritas Snorkel, Double Dip, Dolphin Watch, Ultimate Express, and Island Adventure.  Discounts are not valid with any other offer. One coupon per group. Blackouts and restrictions may apply, 888-976-0899

GET PAINTED AT PARADISE TATTOO

Featuring some of the best tattoo artists the world has ever seen with special assistance from Sean Avram of Skin Wars.   

Make this year's Fantasy Fest complete as you sport your favorite body paint shades and designs with water and sweat proof paint, glo paint, ink or wild costume accessories. Paint anything and everything from whole body to finger painting, Plus enjoy great deals on Bud and Bud Lite. Daily 10 am - midnight, 627 Duval St.; 305-292-9100

HAIR OF THE DOG AT ISLAND DOG 

If you wake up with more of last night's partying then you want to, get cured with the Hair of the Dog and stroll over to Island Dogs where huevos rancheros and breakfast pizza and bottomless mimosas can help take the fuzz off your fizz.

So, it's the morning after and last night's shenanigans are a bit fuzzy? Well, take the walk of shame over to Island Dog.  Daily from 9 am - 1 pm, 505 Front St.; 305-509-7136

HOT TIMES AT PEPPERS OF KEY WEST

The heat is on and in more ways then one!  Sample over 100 flavors of sauces at Peppers of Key West free tasting bar!  You can also grab a bottle of the Fantasy Fest special edition cayenne pepper sauce for your next party at home!

2 locations: 602 Greene St. 10 am - 8 pm and 500 Truman Ave. 10 am – 8 pm, 305-295-9333

IVS IN THE KEYS DUVAL CRAWL CURE ALL 

If you have partied way to much and are paying the price don't worry about missing out on any of the wild raucous fun.  IVs in the Keys are your cure and after 45 minutes of hydration therapy you'll be ready to rock the town and the night away! 

Office rehydration available during Fantasy fest at 531 Whitehead St, 305-395-8245.  Don't forget the last 2 days of Fantasy Fest you'll want to end the partying with a bang SO make a 'rescue stop' at the Street Fair booth Friday and Saturday, October 25 - 26 and get revitalized! 

REDDY ICE FANTASY FAÇADE ™ COMPETITION

Festively decorated homes and businesses compete for money. For info call the Fantasy Fest office 305-295-9112

SOUND CHECK AT THE GREEN PARROT

Get a head start on the party spirit and a sneak preview of the rocking good times ahead later at night by visiting the Green Parrot daily between 5:30 pm - 7 pm, 601 Whitehead St., 305-294-6133



Friday, October 18, 2019 Schedule of Events

GOOMBAY FESTIVAL AT BAHAMA VILLAGE AT DUVAL AND PETRONIA

Fantasy Fest kicks off with this family event in Key West's Bahama Village.

This annual Key West party features local arts, crafts, plus an assortment of tantalizing foods. You'll also want to visit the main entertainment venue on the Truman Annex located at Petronia and Fort where the nonstop pulse of various music genres will keep the party's beat moving. Noon to midnight; FREE

HAVANA CABANA POOL PARTY!

Bring your swimsuit and party on at the Havana Cabana at Key West's largest pool!  Tantalizing Cuban food, along with refreshing drinks, games and more available from noon pm - 5 pm, DJ music from 1 pm - 5 pm, 3420 N. Roosevelt Blvd., 305-294-5541, FREE

ROYAL CORONATION BALL

Benefiting AH of Monroe, Inc, this year's annual event features a 2 hour stage show, "Rock & Royalty".

Suggested donations for general admission is $10, reserved seating has an additional fee. Includes 3 course plate dinner, cash bar available. 6 pm - 10 pm, Key West Amphitheater, Truman Waterfront, 21 E Quay Rd, 305-296-6196

FREAKY TIKI PARTY

Start off this years Fantasy Fest with Freaky Tiki! D Gyver gets freaky with the Retro Freaks & Tiki Geeks of all shapes and sizes plus Sideshow Monsters, Oddities, and More.  430 Greene St, 9 pm - late



Saturday, October 19, 2019 Schedule of Events

GOOMBAY CONTINUES!

Fantasy Fest kicks off with this family event in Key West's Bahama Village.

This annual Key West party features local arts, crafts, plus an assortment of tantalizing foods. You'll also want to visit the main entertainment venue on the Truman Annex located at Petronia and Fort where the nonstop pulse of various music genres will keep the party's beat moving. Noon to midnight; FREE

CORAL HEAD BLUES FEST - MARATHON FL

Benefiting veterans and local charities, this Music Fest sets the mood for a week of fun and partying. Sponsored by the American Legion of Marathon you'll be transported by the epic sounds of Blues artists from International, National and local arenas.

Gates open at 11 am, with an All Star Jam at 9 pm. Reduced pricing for advance tickets. Festival seating so bring your own blankets, no pets except for service animals, Community Park Amphitheater, 200 Ocean, 36th St, Marathon FL.

Tickets and event information available at:

https://www.etix.com/ticket/p/6288740/coral-head-bluesfest-marathon-marathon-community-park

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Regular seating - $55, $75. Doors open - 6:30 pm, Show - 7 pm.

Tickets and information available at https://www.waterfrontplayhouse.org



Sunday, October 20, 2019 Schedule of Events

LA TRATTORIA OCEANSIDE PRESENTS ZOMBIE BRUNCH

Enjoy an all you can eat Zombie Brunch just 2 blocks from the East Martello where the Zombie Bike Ride is held next!

Parking available for bikes and cars. 3593 S Roosevelt Blvd, Reservations: 305-295-6789, 9 am - 2 pm

ZOMBIE BIKE RIDE (NO NUDITY PERMITTED)

This family friendly event focuses on newly awakened zombies who have recently risen from dead.

Join other zombies who are congregating at their newly appointed Zombieland at the East Martello Tower.  2:00 is the appointed time to rise from the dead and show off painted bodies while mid afternoon snacks are served from 2 pm - 6 pm. After, the cavalcade of zombies will hop on bikes and ride down Hwy 1 to Duval Street to hook up with throngs of other zombies at the Key West downtown Zombiefest.

Register at https://www.zombie-bike-ride.myshopify.com, $5 Entry Fee 

ZOMBIEFEST OFFICIAL AFTER PARTIES

Zombie fun doesn't stop after the Zombie Bike Ride's party is over! Partying continues all night long, stop by these official party places: Bagatelle, Green Parrot, Irish Kevin's, Mangoes, Sloppy Joe's, and Tiki House.

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

Tickets and information available at https://www.waterfrontplayhouse.org




Monday, October 21, 2019 Schedule of Events 

THE PERRY HOTEL'S RINGMASTER’S POOL PARTY

Fantasy Fest steps into the ring - circus ring that is!  Featuring circus themed drinks and food, plus music by popular local favorite Patrick & The Swayzees, you'll quickly get into the party mood. Noon - 4 pm, 7001 Shrimp Rd, 305-296-1717, $10/person

BEATLES TRIBUTE NIGHT AT THE GREEN PARROT

Put on your '60's best or dress as one of the Fab-4 as you reminisce, sing, dance and party to Jeff Clark and Tony Baltimore and their Fab Four Show "The Beatles, All You Need is Love". 5:30, 9 and 11 pm, 601 Whitehead St., 305-294-6133

HEROES AND VILLAINS 5K RUN/WALK

Walk, run, fly or crawl! But make sure you're super, evil, and AWESOME! Don your best Super Hero or Super Villain costume and get set to flash to the finish line at 6 pm.  This popular 2019 Fantasy Fest's event also awards to the first 400 heroes or villains who register, a puzzle piece finisher medal featuring the famous 90 Miles To Cuba buoy. 

This Key West event begins 6:00 pm at the Southernmost Beach Cafe located at 1405 Duval St. and follows with the celebratory Sunset Luau & Pig Roast. Registration information: https://www.themeruns.com/heroes-and-villains-5k-key-west

SOUTHERNMOST POST HEROES AND VILLAINS RACE LUAU 

Starting at 6:30 pm toast the winners of the Heroes and Villains 5 K Run/Walk and then celebrate luau style at this Key West beach party where music, food, and fun top the list. 

Savor an authentic Caribbean style buffet featuring tantalizing Roast Cuban pork with picadillo, frijoles negros, soffritto rice, yuca fries, tostones and desert. 1405 Duval St., 305-295-6550, 6:30 pm.  $45 includes one drink per person. Tickets: keystix.com

MARTINI MONDAY

To celebrate Fantasy Fest in style you need a martini and what could be better than ALL Martinis for just $7.00.  Food and live music top off the fun as you party at Virgilio's, La Trattoria Old Town, 

524 Duval Street. Bar opens 6:00 pm

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

Tickets and information available at https://www.waterfrontplayhouse.org

WOMANKIND BRAZAAR: LIVE AUCTION SUPPORTING WOMEN'S HEALTH

Dress for the 70's at this year's traditional and fun bra decorated fundraiser. Featuring 1970's game show motifs plus game show host and participants (you?), fun surprises and yes - booby prizes.  Beautiful hand crafted bras by gifted artisans are available for sale plus enjoy the fun at the pre-auction disco featuring tasty drinks and treats.

Key West Theater, 512 Eaton St, 7 pm - 10 pm

KINKY CARNIVAL

If you're not dressed in your best kinky costume you're not getting in to the original and best kink party Key West has to offer. Open bar 8 - 11 pm. $35 tickets on sale Saturday October 20 at First Flight, 301 Whitehead St, email: jackie@keysrestaurantsgroup.com

MUSTACHE MONDAY AT DURTY HARRY'S

Calling all mustaches, real, applied or penciled and head to Durty Harry's for a night of rocking music and great drinks.  Plus enter the contest for the most outrageous 'stach'! 202 Duval St., 305-296-5513, 8 pm

SLOPPY JOE’S COMIC BOOK CAPE-ERS

Dress up as your favorite caped superhero or super villain and get a chance to win Sloppy Joe's gift cards for the best costumes! Party starts at 8 pm, costume judging and awards at 9:30 pm, live music 10 pm, 201 Duval St. 



Tuesday, October 22, 2019 Schedule of Events

BEACH BASH 

Enjoy the fun at Southernmost Beach Cafe's South Beach located at 1405 Duval St., 305-295-6550.  Dance and play in your sexiest beach wear while you revel to the rockabilly music of Patrick and the Swayzees. Enjoy a variety of drink and food specials and party the afternoon away at this hot Key West outdoor event!  2 - 5 pm

OFFICIAL FANTASY FEST POSTER SIGNING PARTY

Participate in the meet and greet party for the 2019 winner of the poster contest.  Enjoy tasty libations provide by WineO where posters are also available for purchase. La Concha Hotel & Spa, 430 Duval St, 305-296-2991, 5 pm

TUTU TUESDAY PRE-PARTY WALKING PARADE BAR CRAWL

The pre-party for all tutu wearing prom party goers begins at The Porch with a TuTu Prom Parade! Party as you parade through downtown Key West and make a few fun stops along the way. 

Walking Prom Parade Floats encouraged (no motorized floats please!). 

Parade stops include: Mary Ellen's, First Flight,Tiki Bar, Shots & Giggles, General Horseplay and Rick's for TuTu Fun!

Registration and pre-party at Mary Ellen's: 5:30 pm, Tutu Pre-Prom parade: 6:30 pm, 420 Applerouth Lane, 305-916-5816. $35 person and includes shots at all stops PLUS required tutu party wrist band ($20). Wrist bands are given at the Porch pre-party at Mary Ellen's and no Tutu prom party admission is allowed without the wrist bands or tutu.

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  

Tickets and information available at https://www.waterfrontplayhouse.org. Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

11th ANNUAL TUTU TUESDAY

Fun is what it's all about as TuTu lovers and wearers join in the celebration of the multi-functional and endearing TuTu.  

Beginning October 20, tickets available at General Horseplay. Doors open: 7 pm, General Horseplay Complex, 423 Caroline Street, $20 Wristband Admission. 

COCKTAILS FOR ANIMAL TAILS!

Don't miss out on the fun while benefiting a true worthwhile cause - the Florida Keys SPCA.  Help the animals while having a blast at any or all 8 of Rick's Bars featuring an "All You Can Drink" party for $35.  Each bar in the Rick's Key West bars complex have been morphed into a different Animal Kingdom Around The World.  

Don your favorite set of ears and tails so you can appropriately party like the animal you are! 

Pre-sale tickets available from fkspca.org. (click on Donate then Cocktails Tickets) or at 5230 College Rd.,305-294-4857.

All proceeds benefit the animals of the Florida Keys SPCA. $35 - All You Can Drink, Rick’s Complex, 202 Duval St.,  7 pm -10 pm

MEN OF LABARE TIGHTY WHITEY PARTY

Magic Mike made the Men of Labare famous and now you can cheer, and applaud the hottest all male review!  

Sexy white wear is the preferred costume choice and couples are welcome at this event held at Bottle Cap, 1128 Simonton St., 305-304-1188. Ticket availability is limited tickets so don't miss out and get your tickets now at www.keystix.com. Fee, 8 pm

CAPT. TONY'S PARTY IN PLAID

Join the exotic fantasy party with a plaid theme designed to provoke your wildest dreams or naughtiest of fantasies.  Music, drinks and fun at 428 Green St., 305-294-1838, No Cover Charge, 8 pm

GREEN PARROT GREEN PARTY - IT'S NOT EASY BEING GREEN!

Wear green and or think green as in recycling!  Go wild and put together a costume that reflects any or all of the above, no matter how zany or sexy!  Plus party on to the music of Patrick and the Swayzees.  601 Whitehead St., 305-294-6133, Shows at 10 pm and midnight.



Santa and His Reindeer
State Archives of Florida, Florida Memory




Wednesday, October 23, 2019 Schedule of Events

WASTING AWAY AT THE ORIGINAL MARGARITAVILLE

Why not kick start your day by joining in the fun at The Original Margaritaville? Dress like a tourist, and enjoy the libations as we celebrate each hour with a new flavored drink and different colored lei! 500 Duval Street 305-292-1435. 11 am til closing

ROCK AND ROLL REVITALIZING 1960'S POOL PARTY

Step back into a psychedelic time when life was simpler, more fun, and filled with fanciful things such as Tom Collins, and Pink Squirrels.  Remember the blushing excitement of wearing a bikini for the first time, or when mini-skirts were the hottest new wave in fashion.  

So grab your coolest outfits and take a step into the past, to the dawn of the Rock 'N Roll era!  Head over to the Marker Waterfront Resort and groove to Patrick and the Swayzees performing poolside.  Sip on a myriad of colorful libations, and rock the afternoon away. 200 William St., 1 pm - 4 pm, 305-501-5193.

PET MASQUERADE & PARADE

This annual Key West favorite, gives owners and animals a chance to dress alike and show off while strutting their stuff.  

Seating is free or bring blankets and/or chairs.  No coolers please. Food and beverages are available at event.

Benefits Lower Keys Friends of Animals; Key West Amphitheater, Truman Waterfront Park, 21 E Quay Rd For more information email petmasquerade@hotmail.com. 

Registration for competition at 4 pm, show at 5:30 pm. $25 per entry, with 4 categories available, FREE to watch

Benefits Lower Keys Friends of Animals; Casa Marina Resort; 1500 Reynolds St. For more information call 305-304-1026 or petmasquerade@hotmail.comand for VIP seating contact www.keystix.com

CUSTOM HOUSE PERFORMANCE ART

Key West street performers entertain at the old Custom House, thrilling onlookers with their amazing and unusual talents. 281 Front St., 305-295-6616, 5 pm - 7 pm 

CHERAOKE

Cher, widely considered he Queen of the universe and everything else is honored at this special event which also includes a Cher look a like contest with prizes! Join in the Cher Karaoke (Cheraoke) fun while sipping themed cocktails and enjoining Cher trivia. 

Rum Row, The Gates Hotel, 3824 N. Roosevelt Blvd; 5 pm - 8 pm, 305-320-0930, FREE

MOTOWN "LET'S GET IT ON" DANCE PARTY

Get Down with Motown with The "Soul Man" Robert Albury Band and Patrick and The Swayzees!  

Sunset Pier, 0 Duval St., 6 pm - 11 pm, FREE 

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

Tickets and information available at https://www.waterfrontplayhouse.org

SMOKIN' TUNA HOMEMADE BIKINI CONTEST BY FREE LIBATIONS

More than $5000 in cash prizes with $2000 being awarded to first place winner who displays the most creativity in costume design.  Judging is based on the hottest, sexiest AND most original costumes! 

Doors open at 7 pm and contest starts at 8 pm.  $10 registration fee, VIP tickets available at 305-517-6350 which also includes open bar, snacks and a meet and greet with the sexy contestants! 4 Charles St., FREE general admission.

WHARFSTOCK AT THE SCHOONER WHARF BAR

Get groovy and dress as if you were in Woodstock but here, best hippie chick and grooviest dude win prizes! Party starts at 7 pm; judging for prizes at 8:30 for dreamiest hippie chick and grooviest dude. Music from Gary Hempsey and That Hippie Band from 7 pm - midnight, 202 William St.; 305-292-3302, FREE (no cover charge or entry fee)

LUCY'S BLUE PARTY

Coolest Key West bar and restaurant fires up the action with their sexy, blue marine themed costume party.  Best blue costumes will receive the best prizes! Starting at 7 pm - 10 pm, dance the night away to the Marshall Morlock Band and for those super late night party owls, music is provided by a DJ from 10 pm - 2 am! 

Enjoy house designed drinks, prizes and lots of fun! $5 entry fee, 7 pm, 221 Duval St.

TARZAN-N-JANE AT THE GREEN ROOM

Jungle antics are a-plenty at The Green Room this year! Dress up in your favorite jungle-garb and let your inner beast shine through as you enjoy the drinks, and great music at this party animal Key West event! 

Enter the "Ruler Of The Jungle" contest and vie for 1st, 2nd or 3rd prize. $10 entry fee, must be 21+ to enter. 501 Greene St., 8 pm with contest winners announced at 11 pm.

8th ANNUAL LUV2GLOW PARTY

Prepare to experience the best of everything: dark, glowing sexual pulsating heat as you embrace the excitement at Mary Ellen's Bar LUV2GLOW party.

When the lights go off, bodies glow, writhe and whirl to the best dancing music around. Party with hot Bartenders and sexy glo-go dancers at pulse pounding, sexy, neon glowing Key West Fantasy Fest event! Rumor Lounge; 420 Appelrouth Lane, 305-916-5816, 9 pm, Fee

SEXY BULL RIDING CONTEST

Cowboy Bill’s incredible Fantasy Fest Ladies Nite Party!  Free well drinks for ladies from 9 – 11 pm and free draft beer all night. 

Midnight the heat cranks up as sexy ladies battle it out during Cowboy Bill’s Infamous Sexy Bull Riding Contest. Contest has a guaranteed $750 in cash PLUS the prizes will go higher as the night goes on! Sit back and watch as 20 of the hottest ladies dare to ride the bull for cash and prizes!

Limited tickets available for special VIP lounge. 305 292-1865 or email cowboybillkw1@gmail.com, FREE Admission, 618 Duval St. Free drinks start at 9 pm

FOGARTY'S RED PARTY 

Everything is RED at Fogarty's including costumes then party the night away to DJ provided music!  Make sure you've got your craziest, wildest, even skimpiest 'red' on, then enter the zany costume contest! Tickets can be purchased in advance at Fogarty's, 277 Duval Street, 305-294-7525, 9 pm. 

DUNGEON OF DARK SECRETS AND FETISHES

This is where you get to party it up, play, watch, or join a show BUT always dress to thrill at the only true Fantasy Fest Fetish Party. You're only limited by your imagination when it comes to naughty attire.

Wear as little or as much as you dare: leather, uniforms, levis, underwear, vintage, glam, PVC, latex, cyber, burlesque, masks, or whatever tempts and thrills you.

801 Bourbon Bar/Saloon 1; 801 Duval St., tickets available at door, VIP tickets guaranteed to sell out fast so for more information call Brad at 305-731-9055. 9 pm

ABC (ANYTHING BUT CLOTHES) PARTY 

Enjoy the fun as celebrity Flavor Flav hosts this totally risque party.  $700 in cash and prizes are awarded to entrants with the most outrageous and creative costumes/body painting.  

Tickets are limited to this insanely outrageous ABC (Anything But Clothes) Party held in the adult entertainment club setting at Sandbar Sports Grill, 511 Greene St.  Get tickets while available at www.keystix.com, 305-304-1188, 10 pm




Thursday, October 24, 2019 Schedule of Events

IRISH KEVIN'S ANNUAL 80's PARTY 

Travel back to the 80's and rock and roll all day long at this hot Key West party! Get out your leg warmers and Members Only jackets, dress head to toe in stylish, sexy 80's attire!

Live music with prizes given all day, then get ready to really rock from 10:30 pm til dawn as an 80's Rock Band sets the night on fire!  211 Duval Street; 305-292-1262; Awards given all day, 80's band starts at 10:30 pm; Fee

BERKSHIRE HATHAWAY OPEN HOUSES

Don't miss out on a chance to win 4 tickets to their annual Parade Party by signing up at any of the open houses during the Parade of Homes Mega Open House Event, October 23 and 24, 11 am - 3 pm.  Party to be held at the Berkshire Hathaway Knight & Gardner Realty office located at 336 Duval St.

NAUGHTY BIKE RIDE

Naughty makes nice friends on this Naughty bike ride down Duval. Body paint, drinks, loads of fun!  Bike registration online and tickets will be limited. 

Bikes or PediCabs are available: Single Bikes are $65, Pedi Cabs are $150 (with a Bottle of Champagne) plus open Bloody Mary and Mimosa Bar from 11 am - 1 pm.  Registration and Pre-Party: 11 am – 1 pm.  Registration plus body painters, music, food and open Bloody Mary & Mimosa Bar in parking lot at 803 Duval Street. 

Then party as you bike ride to Smokin' Tuna where you'll enjoy free admission to the concert with Joel Rush, Caffeine Carl & The Buzz. Bike pickup is upon arrival so no returns required. 305-294-4737, tickets available at keystix.com

FAMOUS KARAOKE AT TWO FRIENDS PATIO

Dress up as your favorite singer or group and then sing it up at Key West's Oldest Karaoke bar. Prizes awarded for costumes and singing, plus happy hour specials offered. Two Friends Patio, 512 Front St.; 4 - 7 pm, no cover

DANTE'S 13TH ANNUAL HALOS & HORNS POOL PARTY & WET T-SHIRT CONTEST

Get Wet and wild for a chance to win big money at Dante's where this Key West pool party goes from noon to 6 pm. 

Free body painting, live music, giveaways, food and drink, plus prepare to be even more thrilled with the erotic pole dancing that begins at 4:30 pm. 

Dante's Restaurant & Raw Bar; 951 Caroline St, next to the ferry terminal. www.danteskeywest.com, 305-293-5123, FEE

CUSTOM HOUSE PERFORMANCE ART

Key West street performers entertain at the old Custom House, thrilling onlookers with their amazing and unusual talents. 281 Front St., 305-295-6616, 5 pm - 7 pm 

KICKING IT OLD SCHOOL AT CONCH TOWN

Dress in your best or sexy overalls and prepare to mingle with the locals as you enjoy Key West's best drink prices and great DJ music. $10 at the door, proceeds benefit Arnold Wayne Dunlop II Scholarship Fund. 

Prize awarded for best costume. Conch Town Liquor & Lounge, 3340 North Roosevelt Blvd, 305-296-4343, 6 pm.

37th ANNUAL HEADDRESS BALL

Follow the searchlights to the Truman Waterfront's new Key West Amphitheater at the end of Southard St as the popular gay and lesbian Key West Fantasy Fest event unfolds with dancing before and after the Ball.

Don your fanciest feathers, fruits, and other exotic headdress attire and vie for this year's fantastic prize of $3000 for best headdress.

This fundraiser for the Key West Business Guild sells out early so buy tickets online after June 1st at www.keystix.com so you don't miss out! Doors open at 6:30 pm and the show goes on at 8 pm.  Tickets sell out early, keystix.com

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

Tickets and information available at https://www.waterfrontplayhouse.org

ROCKABILLY "SHAKE, RATTLE & ROLL" PARTY AT SUNSET PIER

Feel the beat as you party away to great music at the beautiful Sunset Pier.  Duval St., 7 pm - 11 pm, FREE

SLOPPY JOE’S 40th ANNUAL TOGA PARTY

Held at Sloppy Joe's Key West bar, this is "Still The Best Ancient Roman Party in Town!" Contestants dress in theme inspired togas with a Sloppy Joe's Gift Card giveaways being awarded throughout the night.  

Please note togas are required and body paint does not count as a toga but can be included as part of the costume.

Audience picks winners who receive Sloppy Joe's Gift Cards for 1st - 3rd prizes!

Free to enter contest at this very popular Schedule of Events party. 201 Duval St.; Signup is between 8:00 - 9:15 pm, with ceremony starting at 9:30. Door charge

WHITE PARTY 

Rick's Entertainment Complex is huge and they are now hosting Key West's biggest bash which will have you partying til the wee wee hours of the morning!

Featuring a variety of venues designed to tempt any party goers heart, you'll find nonstop fun as you prowl from bar to bar in this Key West complex of 8 bars.  8 pm, 202-208 Duval St.; 305-296-4890, info@ricksbarkeywest.com

EXPOSED AT THE BOURBON ST. PUB ADULT ENTERTAINMENT COMPLEX

The name says it all. This clothing optional, wildly dare to bare it all outdoor pool, hot tub and foam party is one of the hottest Key West events.  Step inside and you can rock it up at the black out/black light dance party guaranteed to get your adrenaline pumping and more.

Glow Sticks, DJ's, large projector screens featuring favorite fantasies and exotic male and female dancers are just some of the titillating fun you'll have at this hugely erotic 'Bare What You Dare' Key West party.  

Passes will be on sale at the New Orleans House starting October 1st; 8 am - 8 pm. 305-293-9800. 724 Duval St; www.bourbonstpub.com, 9 pm - 4 am

SANDBAR SPORTS GRILL'S 4th ANNUAL BODY PAINT COMPETITION

Body paint - everywhere, anywhere - is the name of the game of this cosplay body paint competition. Plenty of food, fun, booze, and painted flesh to satisfy your hunger, sexual or otherwise. 

$1500 in cash and prizes, sign up available all week. 511 Greene St., first round begins at 9 pm.

FAT TUESDAY PINK PARTY

Come join the party geared to "Save the Ta-ta's!" with the American Cancer Society - Making Strides Against Breast Cancer of the Florida Keys receiving a percentage of the night's proceeds.  Support the cause and don your sexiest pink costume or cover up in supportive body paint!  

Costume contest with a $500 bar tab for 1st place, $250 bar tab for 2nd place, and $100 bar tab for 3rd place. Live entertainment provided and fun party favors included while supplies last  305 Duval St.; FatTuesdayPinkParty; 305-296-9373; 9 pm; Fee

COWBOY BILL'S GIT-R-WET T-SHIRT CONTEST

Don't miss out on the fun as 20 of the hottest ladies model the sexiest, most unique wet t-shirts and vie for $1K prize. Featuring drink specials, VIP seating, for info on general admission and VIP tickets email cowboybillkw1@gmail.com, 618 Duval Street, 305-292-1865, 10 pm

PAJAMA AND LINGERIE PARTY

Heed Mr. Playboy as he urges everyone to attend this popular event wearing the sexiest lingerie or PJ's! Don't forget to enter the $700 Hugh Heffner - Marilyn Monroe look alike contest and mingle with celebrities.  

Tickets sell out fast. Purchase advance VIP tickets online at www.keystix.com; BottleCap Lounge; 1128 Simonton St.; 305-304-1188;  10 pm; Fee

FUN HOUSE

Prepare to be thrilled as the Rainbow Circus acrobat performers treat you to a true extravaganza. Enter at 423 Caroline St and 218 Duval St. 21 and up, costumes encouraged, $10 cover charge. 

THE HISTORY, CULTURE, AND POLITICS OF SEX

TBA



Friday, October 25, 2019 Schedule of Events

NOCHE LIBRE

The greatness of Cuba's past is cause to celebrate so grab your best Cuban garb, get your dance moves on and prepare to win prizes at the Havana Cabana Salsa Dance Off! 

Pool side, enjoy live music from 1 pm - 5 pm, plus sample 15 different types of mojitos designed to quench your thirst!

This is a party with something for everyone, games, great food, awesome drinks, free giveaways, plus FREE admission. 3420 N. Roosevelt Blvd, 305-294-5541, Noon - 5 pm.

BOWTIES & BIRTHDAY SUITS! - ISLAND HOUSE FOR MEN

This is the only gay all male Key West event and it's geared up to indulge ALL of your wildest pool party fantasies!

Admission includes bowtie, complimentary cocktail, free resort privileges until Saturday 8 am.  DJ music, go-go male dancers, great food and drinks, and luxury resort living.  

Tickets available in advance at keystix.com, or at the door.  Photo ID required for all entrants, 1129 Fleming Street, 305-294-6284, FEE, Noon til ?

A FANTASY FEST STREET FAIR

Duval Street is famous as a party place and now this popular mile-long Key West street adds another element of fun by featuring a fair. Don your favorite costumes and enjoy a variety of arts and craft, with plenty of food and drink for everyone.  Noon to 10 pm FREE

DAY AT SOUTHERMOST PLAYBOY MANSION - BEACH BUNNY POOL PARTY BASH

This Playboy Bunny Infinity Pool Party is designed to get your juices flowing. Great music, spectacular view from the breathtaking pool, drinks, even topless sunbathing as long as you wear your bunny ears!

1400 Duval Street, 305-296-3141, Noon - 5 pm, $25 admission

BOURBON ST. PUB TEA DANCE

Don't miss out on this riotist 'tea in the street' party.  Come mingle with celebrities, elaborately attired drag queens, and dancers plus pool parties Friday and Saturday in back of Bourbon. 724 Duval St., Noon - til ?; 305-293-9800; FREE

CUSTOM HOUSE PERFORMANCE ART

Key West street performers entertain at the old Custom House, thrilling onlookers with their amazing and unusual talents. 281 Front St., 305-295-6616, 5 pm - 7 pm 

MASQUERADE MARCH

Don't miss out on one of the most popular Fantasy Fest Schedule of Events!

Starting at the Frances Street entrance to the Key West Cemetery, revelers party and dance along the march route, enjoying time out at select inns to sample tasty libations designed to sooth parched throats and keep the party moving forward.  March begins at 5:30 pm; All welcome; FREE

A BURLESQUE PARODY - ROCKY HORROR PICTURE SHOW

October 19 - 25, don't miss out on this exciting 7 night theatrical extravaganza at the Waterfront Playhouse located at 310 Wall St.  Doors open - 6:30 pm, Show - 7 pm. Regular seating - $55, $75.

Tickets and information available at https://www.waterfrontplayhouse.org

13TH ANNUAL PIRATE BASH NOW AT TURTLE KRAALS!

Ahoy landlubbers! The Rum Barrel pirate crew has sailed over to Turtle Kraals and wants you to join the fun which includes the traditions of drinking and dressing like a pirate!

More than $1500 in cash prizes for the best pirate and wench costumes. Enjoy great rum libations, and shake your pirate booty to great DJ music.  Doors open at 7 pm, costume contest starts at 9 pm. Turtle Kraals, 231 Margaret Street, 7 pm, $10. For more information call 305-294-2640

MASQUERADE MARCH AFTER-PARTY WITH THE GREEN PARROT UKULELE ORCHESTRA BAND

Key West Old Town's Masquerade March Madness continues at 7:30 pm as the The Green Parrot Ukulele Association Band marches down Southard Street and onto The Green Parrot stage.

Come party as this rollicking party continues through the streets, then party on into the Green Parrot where things continue to wind on into the early morning hours! 601 Whitehead St.; 305-294-6133, 7:30 pm

PLAYING GAMES WITH LADY LETHE

Let the kinky begin!  Lady Lethe will stun you with an unimaginable performance that will leave you spell bound and demanding more! 801 Bourbon Bar, 801 Duval St. Doors open 7:30 pm, Show at 8 pm



19TH ANNUAL LIVING ART AIRBRUSH EXPO

Artistic expression on the human body has contestants competing for more than $3000 in prizes and cash.

2019 Fantasy Fest contest categories: best female canvas, best male canvas and best couple/group canvas. Painting and partying with drink specials and live entertainment. 

VIP's are able to vote for their favorite contestant, plus access the backstage VIP section's open bar, snacks plus contestant meet and greet.  VIP Tickets available at www.keystix.com or Sunset Pier Bar.

To enter call Sunset Pier at 305-295-7047 or email at dining@oceankey.com. Sunset Pier at Ocean Key Resort, 0 Duval St., Doors open at 8:00 pm; Contest at 9:30 pm 

To enter call Sunset Pier at 305-295-7047 or email at dining@oceankey.com. Doors open at 8:00 pm; Sunset Pier at Ocean Key Resort, 0 Duval St.

GLITTER AND GLOW PARTY

Glitter with the right black light makes you glow - hot, sexy glow! Sparkling hot and glittery magic as the DJ kicks the party up! Drink specials starting early! Sidebar Key West, 504 Angela St., 305-294-0555, 8 pm - 4 am

THE GREAT GATSBY

Relive the elegance and wealth of this great era brought back to life with a Key West twist.  Enjoy great music and drinks, while participants with the magician's costume compete for prizes.

Costumes ARE required. Club A, 218 Duval St., $10 cover fee, doors open 9 pm

PIMPIN AIN'T EASY / PIMP AND HO PARTY

Enter the $700 Mr. Pimp and Ms. Ho costume contest, Hosted by Ron Jeremy, this event is guaranteed to sell out. Purchase advance VIP tickets online at www.keystix.com; Sandbar, 511 Greene St; 305-304-1188; 10 pm, FEE

KINKY COUPLES PARTY (Hosted by RubberDoll)

This official SDC event is the one and only exclusively Adult Couples event and is open only to registered and approved couples in proper Fantasy Fest and costume attire. The full service bar and a discreet downtown location along with great music makes this a favorite couples event.  

Thrill to a world class performance by RubberDoll, the highly acclaimed festish latex performer, then plan on partying until the wee hours of the morning. Tickets are limited and are available online only www.keystix.com; 305-731-9055, 801 Bourbon Bar, 801 Duval St., 10:30 pm - 4 am 

SAN CARLOS STREET PARTY

TBA - 516 Duval St.; 305-294-3887



Saturday, October 26, 2019 Schedule of Events

BOURBON ST. PUB'S VIP PARADE BALCONY BASH

Don't miss out on the fun or one of the best views of the Fantasy Fest parade on Duval St. This is THE VIP, high-end open bar, catered party, with private entrance and restrooms. No guaranteed reserved spaces. 150 guests only. 724 Duval St.; neworleanshousekw.com, 305-293-9800, keystix.com; FEE 8 am - 8 pm

BOURBON ST. PUB POOL PARTY

Music entertains, drinks soothe as you play in the pool or lounge in the jacuzzi. 

724 Duval St., 305-294-9354, Clothing Optional, Noon til ?

DUVAL STREET PROMENADE

Drink, eat, dance and party your way on the march from the Gulf to the Atlantic. Noon to 10:30 pm; FREE

PRE-PARADE PONG PARTY

If you like ping pong and competition, the 24 North Hotel is the must pool party for you! Different tables, lots of beer and food available, plus music to keep you pumped and primed. Top team wins a $50 bar tab! 3820 N. Roosevelt Blvd, 305-320-940, 1 pm - 4 pm, FREE Entry

VIRGILIO'S & MARY ELLEN'S FANTASY STREET PARTY

THE block party of the day is here at Applerouth Lane! DJ music, games, plus a 16 foot tall martini glass you can pose next to!  Enjoy fantastic drinks, great food, and tons of fun.

Virgilio's, 524 Duval Street, 305-296-1075, Mary Ellen's 420 Applerouth Lane, 305-294-7750, 3 pm

WOMAN’S CLUB PREMIER PARADE VIEWING PARTY

Dress as your favorite Boardwalk token and enjoy the elevated view of the Parade. Tantalizing appetizers, gourmet dinner, and top shelf open bar served. Hellings House Museum, 319 Duval St., Tickets $250 - $300, Party starts 5:30, parade 7 pm

FANTASY FEST PARADE BALCONY VIEWING PARTY

Parade viewing on Duval's Street largest balcony is guarateed to be the talk of the town.  With an open bar, snacks and beads to throw to the throngs below, you're sure to enjoy the spectacular view and fun. Tickets will sell out early, Bourbon Bar - 801 Duval St.; Tickets: keystix.com and details call Brad 305-203-3461

FIRST FLIGHT PARADE VIEWING PARTY

Enjoy a mouthwatering buffet meal, 3-hour Open Well Bar (domestic beer, house wine & well drinks) and a roof top seat to watch the parade. Assigned seating is on a request, first come - first serve basis.  

To reserve tickets call Jackie, 305-293-8484. 301 Whitehead St., 6 pm

LUCY'S FANTASY FEST PARADE VIP BALCONY VIEWING PARTY

Rocking good times and great parade viewing are at Lucy's!  VIP passes are $250 and include: Premium bar,  food and private restrooms.  Balcony space is limited so get your tickets soon! Doors open 6 pm

ROOFTOP CAFE'S PARADE NIGHT PARTY

Settle in for a night of food, drinks and fun as you dine in comfort and prepare to watch the Fantasy Fest Parade from the birds eye second floor patio of the Rooftop Cafe. 

Enjoy the scrumptious buffet that includes beer, wine and wells drinks for $225 per person plus tax and gratuity. 308 Front Street. For more information call 305-294-2042 or email: info@rooftopcafekeywest.com.  Doors open at 6 pm

MANGOES PATIO PARADE PARTY 

Watch the parade from this elevated vantage point while enjoying drink specials and selected dinner menu all for $30 advance seating, or $40 door admission.  700 Duval St.; tickets at: mangoeskeywest.com.

For private party reservations available in the VIP upstairs balcony and Ricky Ricardo Room (30-50 person capacity) email events@mangoeskeywest.com. Doors open: 6 pm, parade starts: 7 pm, 305-294-8002

PARADE VIEWING AT THE HARD ROCK CAFÉ

Party goers will enjoy their high perch and view of the parade while dining on a delicious menu of prime rib and fresh lobster. Contact Diane at diane.eliopoulos@hardrock.com; 313 Duval St.; 305-293-0230. Doors open at 6 pm

BUD LIGHT FANTASY FEST PARADE

Join 70,000 frolicking party goers on Duval street as amazingly splendid glittering floats, marching bands and dancers sweep by. Starts at 7 pm; www.fantasyfest.com; FREE

DIRTY DOCTOR'S AND NAUGHTY NURSE'S PARTY 

Who said going to the hospital can't be fun?  It certainly is when Vivian Jeremy from Brazil and other celebrity models show up for the official parade after party! 

Enter the $700 Dirty Doctor's and Naughty Nurse's costume contest and dress to win!  Tickets available at keystix.com.  Sandbar, 511 Green St.; 305-304-1188; 10 pm 

KINKY COUPLES PARTY

Very limited tickets available at keystix.com.Tickets are on sale ONLY ONLINE! Guaranteed to SELL OUT!!!  801 Bourbon Bar, 801 Duval St.,10:30 pm - 4 am



Sunday, October 27, 2019 Schedule of Events

CHILDREN'S DAY

Fantasy Fest Schedule of Events includes the annual family day held at Bayview Park at Truman Ave. and Eisenhower Dr.; Noon - 5 pm; 305-292-8912

"THE FAT LADY SINGS" TEA DANCE

As the saying goes, "It ain't over 'til the fat lady sings." The final hurrah and the saying of good-byes are held again at the elegant La Te Da Hotel, Restaurant, Cabaret and Bars; 1125 Duval Street from 4 pm to 8 pm, 305-296-6706; $5







Bloody Sailor


Bloody Sailor
Photo Courtesy of Roy Llowarch on Flickr


This year's Key West Fantasy Fest Schedule of Events with its' great Masquerade Balls and other hot Key West parties, will please even the most frequent festival attendee. Remember to get tickets early for the events that you don't want to miss out on. Popular events sell out fast.

Also don't forget to buy the different costumes you'll want to have so you'll fit in for the various planned Schedule of Events parties. If you're not properly dressed you can't attend certain Key West parties, like Sloppy Joe's where you need a toga or you're not admitted.

Plus the Key West Schedule of Events are really the 10 days of 'sexy'. Get the costumes that will make you feel your very best, so you'll feel like part of this huge Key West event instead of just a bystander.





› Schedule of Events







You May See Ads Here






SAVE BIG WITH THESE
KEY WEST DISCOUNTS






Local Weather Zip Codes

Key Largo - 33037
Marathon - 33050
Key West - 33040




Fantasy Fest Pirate Costumes